Enantio-, atrop-, and diastereoselective macrolactonization to access type III cyclophanes DOI Creative Commons
Jiaming Wang, Kang Lv,

Yilu Wen

и другие.

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Апрель 3, 2025

Язык: Английский

An Assembly of Pyrano[3,2‐b]indol‐2‐ones via NHC‐Catalyzed [3 + 3] Annulation of Indolin‐3‐ones with Ynals DOI
Xia Wang, Shulei Zhang, Shaojie Wang

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(13), С. 1487 - 1492

Опубликована: Март 10, 2024

Comprehensive Summary We report herein an unprecedented N ‐heterocyclic carbene‐catalyzed formal [3 + 3] annulation of ynals with ‐Ts indolin‐3‐ones under the oxidation condition affording functionalized pyrano[3,2‐ b ]indol‐2‐ones. The alkynyl acylazoliums via combination a carbene in presence oxidate proved to be important intermediates for success this transformation. This method features broad substrate scope and mild conditions, including axially chiral skeletons suitable substitutions.

Язык: Английский

Процитировано

9

Organocatalytic desymmetrization provides access to planar chiral [2.2]paracyclophanes DOI Creative Commons
Vojtěch Dočekal, Filip Koucký, Ivana Cı́sařová

и другие.

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Апрель 10, 2024

Abstract Planar chiral [2.2]paracyclophanes consist of two functionalized benzene rings connected by ethylene bridges. These organic compounds have a wide range applications in asymmetric synthesis, as both ligands and catalysts, materials science, polymers, energy dyes. However, these molecules can only be accessed enantiomer separation via (a) time-consuming separations (b) kinetic resolution approaches, often with limited substrate scope, yielding enantiomers. Here, we report simple, efficient, metal-free protocol for organocatalytic desymmetrization prochiral diformyl[2.2]paracyclophanes. Our detailed experimental mechanistic study highlights differences the origin enantiocontrol pseudo - para pseudo-gem diformyl derivatives NHC catalyzed desymmetrizations based on whether key Breslow intermediate is irreversibly or reversibly formed this process. This gram-scale reaction enables follow-up derivatizations carbonyl groups, producing various enantiomerically pure planar [2.2]paracyclophane derivatives, thereby underscoring potential method.

Язык: Английский

Процитировано

9

Divergent Synthesis of Axially Chiral 2-Pyranones and Fused 2-Pyridones via N-Heterocyclic Carbene-Catalyzed Atroposelective [3 + 3] Annulation DOI
Z. Liu, Chenxing Li,

Simiao Zhang

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 24, 2025

An N-heterocyclic carbene-catalyzed atroposelective [3 + 3] annulation of alkynyl acylazoliums with benzothiazole derivatives has been developed for the divergent synthesis axially chiral triaryl 2-pyranones and fused 2-pyridones. The regioselectivity this protocol depends on structure benzothiazoles three different nucleophilic centers. obtained frameworks represent a new class arylheterocycle atropisomers, which may be potentially useful in medicinal chemistry.

Язык: Английский

Процитировано

1

Enantioselective Cascade Annulation of 1,2,3-Triazoles and Enals Enabled by Sequential Rhodium and Oxidative NHC Catalysis Involving Cleavage, Migration, and Cyclization DOI

Xiaoyi Yu,

Hao An, Wenbin Wu

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 28, 2025

The in situ-generated pyrrolin-3-ones serve as novel and versatile synthons, being employed intermediates for the efficient production of pyrrole-fused lactones with high yield excellent enantioselectivity. Herein, we introduce emerging rhodium oxidative N-heterocyclic carbene relay catalysis that enables a highly enantioselective cascade annulation between easily available 1,2,3-triazoles enals. In this proof-of-concept study, engage α,β-unsaturated acylazolium generated from enals via catalysis.

Язык: Английский

Процитировано

1

Kinetic Resolution of Acyclic Tertiary Propargylic Alcohols by NHC-Catalyzed Enantioselective Acylation DOI
Hao An,

Shifei Liu,

Shaojie Wang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(3), С. 702 - 707

Опубликована: Янв. 11, 2024

We report herein an efficient NHC-catalyzed kinetic resolution of acyclic tertiary propargylic alcohols that provides them in high to excellent enantioselectivity. This is the first example realized by enantioselective acylation. The recovered enantioenriched can be facilely converted into other valuable compounds such as densely functionalized and carbmates yields stereopurity. Density functional theory calculations were performed determine reaction mechanism understand origin enantiodiscrimination.

Язык: Английский

Процитировано

5

NHC-Catalyzed Chemo- and Enantioselective Reaction between Aldehydes and Enals for Access to Axially Chiral Arylaldehydes DOI
Zhiguo Zheng, Qian Liu,

Xiaolin Peng

и другие.

Organic Letters, Год журнала: 2024, Номер 26(4), С. 917 - 921

Опубликована: Янв. 18, 2024

A chiral carbene-catalyzed chemo- and enantioselective reaction with racemic biaryl aldehydes α-bromoenals is developed for access to axially 2-arylbenzaldehydes through atroposelective dynamic kinetic resolution (DKR) processes. This DKR strategy can tolerate a broad scope of substrates diverse functionalities. The 2-aryl benzaldehyde products generally afford moderate good yields enantioselectivities. molecules afforded from the current approach are variable simple transformations functional excellent optical purities.

Язык: Английский

Процитировано

5

Recent Advances in NHC‐Catalyzed Chemoselective Activation of Carbonyl Compounds DOI

Yixian Huang,

Xiaolin Peng, Tingting Li

и другие.

Chemistry - An Asian Journal, Год журнала: 2024, Номер 19(9)

Опубликована: Март 7, 2024

N-Heterocyclic carbenes (NHCs) catalysts have been employed as effective tools in the development of various reactions, which made notable contributions developing diverse reaction modes and generating significant functionalized molecules. This review provides an overview recent advancements chemo- regioselective activation different aldehydes using NHCs, categorized into five parts based on modes. A brief conclusion outlook is provided to stimulate novel for accessing functional

Язык: Английский

Процитировано

5

Catalytic stereodivergent and simultaneous construction of axial and point chirality DOI
Wentao Wang, Sen Zhang,

Wenxuan Lin

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(12), С. 3308 - 3319

Опубликована: Янв. 1, 2024

An unprecedented ligand-enabled stereodivergent construction of both N–N axial and point chirality in a single step is reported.

Язык: Английский

Процитировано

5

Carbene-catalyzed enantioselective seleno-Michael addition as access to antimicrobial active Se-containing heterocycles DOI

Hongyan Long,

Sha Zhao,

Chunyan Jian

и другие.

Science China Chemistry, Год журнала: 2024, Номер 67(7), С. 2199 - 2205

Опубликована: Май 28, 2024

Язык: Английский

Процитировано

5

Asymmetric Synthesis of Planar Chiral Carbonitriles and Amines via Carbene-Catalyzed Kinetic Resolution DOI

Ya Lv,

Chengli Mou, Qian Liu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(8), С. 1584 - 1588

Опубликована: Фев. 20, 2024

We have developed a catalytic method using chiral N-heterocyclic carbene (NHC) as the sole organic catalyst to synthesize planar carbonitriles asymmetrically, resulting in optically pure, multifunctional compounds. The demonstrates remarkable tolerance toward diverse substituents and substitution patterns through kinetic resolution (KR) or desymmetrization processes. pure products hold significant potential for applications asymmetric synthesis antibacterial pesticide development.

Язык: Английский

Процитировано

4